


Lipstick and Lace

by CS_impala67



Series: My Kinktober 2020 fics [28]
Category: Supernatural
Genre: Crossdressing, Dean Winchester Wears Panties, Frottage, Kinktober, Kinktober 2020, Lingerie, M/M, Panties
Language: English
Status: Completed
Published: 2020-10-28
Updated: 2020-10-28
Packaged: 2021-03-09 07:36:00
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,169
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27199933
Author URL: https://archiveofourown.org/users/CS_impala67/pseuds/CS_impala67
Summary: He slipped the smooth material up over his hips, the lace trim setting on his trim waist. He adjusted himself in the panties and sighed as the cool fabric cradled his balls. Next came the stockings, that which felt so soothing against his freshly shaven legs. Finally, a pair of 4-inch red stilettos completed the look. He slipped his feet into them, before walking to stand in front of the floor length mirror in his room. He stared at his reflection; The sexy lingerie on his body, and the eyeliner and lip gloss he had applied before he dressed, reflected back at him, and sent a thrill up his spine
Relationships: Castiel/Dean Winchester
Series: My Kinktober 2020 fics [28]
Series URL: https://archiveofourown.org/series/1961551
Kudos: 56





	Lipstick and Lace

**Author's Note:**

> For Kinktober Day 28 I chose cross-dressing/ Lingerie

He slipped the smooth material up over his hips, the lace trim setting on his trim waist. He adjusted himself in the panties and sighed as the cool fabric cradled his balls. Next came the stockings, that which felt so soothing against his freshly shaven legs. Finally, a pair of 4-inch red stilettos completed the look. He slipped his feet into them, before walking to stand in front of the floor length mirror in his room. He stared at his reflection; The sexy lingerie on his body, and the eyeliner and lip gloss he had applied before he dressed, reflected back at him, sent a thrill up his spine.

This was one of his secret indulgences. As a hunter, he always needed to be tough and strong, and he always dressed in a similar fashion, with his flannel, jeans and boots. He liked those clothes, sure. They were practical after all when he was out hunting creatures. But he also secretly longed to feel pretty; to feel more feminine. It was something he warred with himself over, ever since he was a teenager and had seen his first drag queen. He had been in awe at seeing a man in women’s clothes; something he had never seen or even knew was a thing before that day. He remembered wondering what it would feel like to dress like that; to look at himself in a mirror and see someone pretty looking back. He had no desire to go full on drag, or be someone different. He just wanted to be Dean, but sometimes maybe a more feminine version.

The first time he had ever worn a pair of panties, it had been when he was 19 and hooked up with that chick Rhonda Hurley. When she asked him to try on her pair, he had pretended to protest, but inside he had been shaking with excitement. Finally, he would be able to try something he had wanted to for a few years at that point. It had been just as great as he had imagined and he had been sad when he’d had to leave. It took another 15 years for him to get the nerve up to buy himself his own pair of panties, and he’d been slowly branching out from that over the last 5 years. He had a chest in his closet where he kept all of his lingerie and makeup, now that he had a permanent room to store them in secret.

He didn’t often get to indulge in this secret pleasure, only maybe once every few months, but any time the rest of the bunker inhabitants were gone, he pulled out his chest of goodies and dolled himself up. It wasn’t even always sexual, though he couldn’t deny the thrill that went through him whenever he slipped into a sexy pair of panties.

He was so busy checking himself out on the mirror, admiring how the lingerie accentuated his features, when he heard a throat clearing behind him. He spun around startled, and saw Cas leaning against his bedroom door, arms crossed over his chest and an unreadable look on his face.

“Fuck. Shit. I uh…I can explain.” He babbled nervously as he tried to cover himself with his hands. He felt the blush heating his cheeks at being caught like this; his secret now out of the bag. He watched Cas stride closer to him, and closed his eyes tight, waiting for Cas to tell him what a freak he was and that he no longer loved him anymore. He felt his eyes well up and a tear escape as Cas leaned close.

“Shhhh, my pretty little princess shouldn’t cry.” He whispered, breath tickling Dean’s ear, causing him to gasp, both at the sensation and at the words. He pulled back to look into his boyfriend’s eyes, expecting to see mocking in his gaze, but instead he was met with a warm smile and a fond look as Cas reached out to swipe the tear from Dean’s cheek. “What’s wrong beloved?”

“I…uh…I d-didn’t want you t-to see me like this.” He stuttered wetly, tears still stubbornly leaking down his cheeks no matter how much he tried to will them to stop. He was mortified at being caught, and terrified that Cas would leave him, now that he knew Dean’s biggest secret.

“Well, I can’t say I not surprised.” Cas admitted as his eyes roamed all over Dean’s body, taking in what little he was wearing. “I never imagined you could look anymore beautiful than you always do, but it appears I was mistaken.”

“You…uh…you don’t think I’m a freak?” Dean managed to squeak out unsurely, still disbelieving he wasn’t being subjected to a brutal teasing right now.

“Never, my love. You look stunning. Why have I not seen you like this before?” Cas questioned as he dragged his finger over the lace trim of the panties.

“I, uh, I’ve never shown anyone this, uh…this side of myself. Didn’t feel like being made fun of, he.” He laughed humorlessly, still feeling embarrassed and vulnerable.

“I would never make fun of you beloved. I must say, the sight of you in these clothes is very…arousing.” At those words, Dean looked down and noticed the bulge in his boyfriend’s pants. A jolt of arousal went straight to his own cock at the sight.

“What…uh…what are you gonna do about it?” Dean asked breathily as his own cock began to harden, the panties barely containing his girth. Cas just grinned ferally before lifting Dean and throwing him on the bed beside them. He stripped out of his clothes and climbed on the bed gracefully as if he was stalking his prey. He gently removed the heels on Dean’s feet before blanketing the man beneath him. Dean felt their hard cocks brush together, pulling a whine from deep in his throat.

“I can’t wait to make you dirty those panties.” Cas growled in his ear as he thrust his body against Dean’s; their hard cocks grinding together in delicious friction. “They feel so good rubbing against my cock.”

“F-fuck C-Cas.” Dean whimpered as his boyfriend frotted against him, over and over. The panties made it feel incredible and his orgasm was building fast. Before he knew it, his balls pulled tight and he felt himself coming in his panties.

“Fuck Dean!” Cas roared as he followed Dean over the edge, covering the front of the panties in his own release.

They both took time to catch their breaths before Cas moved back and helped Dean out of his panties and stockings and throwing them towards the hamper.

“I believe we may have ruined that pair.” Cas surmised sadly causing Dean to chuckle at the despondent look on his boyfriend’s face.

“Don’t worry Cas. I have plenty more where that came from.” He assured his lover, earning another feral smile from the Angel. They were going to have so much fun.


End file.
